


Lord Stingray Smash Party

by letsmoveourbootybutts



Category: Superjail! (Cartoon)
Genre: Aftercare, Anal Sex, Biting, Chastity Device, Cock Slapping, Come Eating, Consensual Kink, Creampie, Cuckolding, Deepthroating, Exhibitionism, Face-Fucking, Face-Sitting, Facials, Felching, Humiliation, Light BDSM, Light Bondage, M/M, Masturbation, Multi, Multiple Orgasms, Naked Cuddling, Oral Sex, Orgasm Delay/Denial, Rimming, Rough Kissing, Rough Sex, Teasing, Tentacle Dick, Trans Male Character, Verbal Humiliation, Xeno
Language: English
Status: Completed
Published: 2019-06-17
Updated: 2019-06-17
Packaged: 2020-05-13 20:17:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,554
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19258450
Author URL: https://archiveofourown.org/users/letsmoveourbootybutts/pseuds/letsmoveourbootybutts
Summary: The Warden has had Stingray under lock and key for a long time, but now he has a new method of torment he wants to try out, and the twins are very happy to help.





	Lord Stingray Smash Party

**Author's Note:**

> A few notes:  
> The Warden is a post-op trans man. Stingray is non-op.

Lord Stingray had to give the Warden some credit. His aesthetic sensibilities were garish, clashing and reeking of an untoward sense of childlike glee but they were at least consistent in their hideousness. He lay supine in a colossal four-poster bed with lavender satin sheets, wrists and ankles bound with smooth black rope. The walls surrounding him were painted dark purple and covered in lilac illustrations stylistically halfway between Dr. Seuss and ancient Grecian pottery. The subject matter leaned more towards the Grecian in terms of its depravity, endless scrolls of individuals, couples and groups engaged in all manner of sexual activity. All so unbearably tacky. 

The genius interior designer himself stood by the side of the bed, fully clothed while Stingray was completely nude save the belt, with its black leather waist and thigh straps and the shining golden crotch plate and ornate lock. Warden had had this device custom made and spared no expense. It hugged Stingray's body perfectly, the plate airy and comfortable instead of sweaty and chafing. But the comfort of it didn't ease the tight and pulsing desperation welling inside of him.

"So, Stingray, do you know why I brought you here?" Warden asked with a wide smile, jabbing the tip of his cane into Stingrays's chest. 

"For the weekly cleaning?"  

"Dingdingding! Correct! I am going to take off your belt and clean it, and while it dries how does a little bit of flogging sound?"

Stingray forced a smile. "That sounds perfect. By the waaay, how long have I been in chastity? I seem to have lost track of time...."

Warden counted on his fingers for a moment before looking back at his sub with a big grin. "Exactly six months! I think this is the longest streak we've had, it would be a shame to break it now."

Stingray cast his eyes down at the belt. "I suppose so."

"Aw, well, maybe if you're a really good boy today then I can take some of the pressure off. But you lost points just now for being bratty!" He tallied something down in a little notebook before procuring a large ring of keys. Stingray didn't even know what most of them unlocked, but he spotted the key to his cuffs, to his cage, to his specially fitted sensory deprivation hood, etc. However, he did not see the key to his belt. Warden reached the same conclusion, fiddling fruitlessly down the ring. Suddenly, a familiar hum-zap rang through the room. 

"Looking for this?"

There they stood, resplendent in their androgyny, those beautiful bastards the twins. They both wore huge, shit-eating grins across their faces, and the one with the slightly higher-pitched voice held out the tiny golden key. 

"Hey boys!" The warden waved. "I was looking for that in fact! Thank you for finding it! Now, why don't you hand it over?"

The twin holding the key placed it in his mouth, and Stingray gasped in horror at the bob of his Adam's apple, the unmistakable motion of a swallow. 

"So that's how you want to play, huh? I guess you're never getting out of chastity, Stingray." The Warden threw up his hands and gave a pitying smile. "Sorry!"

"Wait, wait, maybe we can make a deal!" Stingray thrashed, trying to position himself in a way that carried some, any measure of dignity. "What would you fine gentlemen desire in exchange for that key?" 

The twins glanced at each other. "Such impudence." "What a brat."

Stingray's eyes went wide and his mouth twisted with panic. "I'm sorry, I'm so sorry. Warden, sir,  please set up a negotiation, please, I need it!"

Warden placed his hand to his chin and thought a moment before snapping his fingers. "How would you boys like to get in on the action? My toy might be a bit bratty but there are ways of softening him up...if you're satisfied with our playtime then can we get our key back?"

The twins made a big show of thinking it over, whispering to each other, looking over Stingray's vulnerable form as he trembled before nodding. "We would be interested." "Let the humiliation begin." And the one who had swallowed the key stepped forward and kissed Warden roughly on the mouth.

Stingray cringed but couldnt tear his eyes off of this interloper plumbing his boyfriend's mouth with a frighteningly long tongue, sliding a gloved hand down his pants and making Warden flush red. He murmered against his throat "Your toy can't pleasure you the way I will pleasure you, Warden."

"Haha, yeah, he is selfish, and weak and  pathetically subby for sure....ooh, goodness. What are you going to do to me?" He tentatively hovered a hand over the twin's ass before getting a nod of permission to stroke it. 

"Take off your clothes, Warden. I am going to rearrange your internal organs."

Stingray watched helplessly as his boyfriend eagerly stripped down,  cock already desperately hard. His own erection strained against the metal plate of his chastity belt and his front hole clenched against nothing, watching this gorgeous twink lay his boyfriend down on the other side of the massive bed, pulling his legs around his waist. The twin had phased his own clothing off, leaving just the boots and gloves, and there was some kind of dripping turquoise tentacle horror emerging from his crotch. The warden giggled and squirmed as the slimy tips tickled against his thighs.

Stingray waited to see how the Warden would transform to fuck the twin. Normally before doing anything with Stingray, the Warden would sharpen his teeth, lengthen his nails and grow his cock huge and imposing. But for the twin, he remained gentle and non-threatening, his dick unchanged from its usual two inches. There was a certain vulnerability about him, a tenderness Stingray had never seen and yet here he was, flaunting it for this smirking twink who was gnawing bruises into his collarbone.

The twin slowly slithered the largest slimy appendage of the bunch into Warden's ass, inch by cautious inch, making the human shudder and cling to his forearms. He pulled his knees tight into the twin's waist, clenched his eyes shut and uttered a whimper behind his bitten lips at the sensation of being probed.   
   
The twin grinned all half-lidded and sly before dragging his gloved hand over the Warden's dick. "Do you like that? I am turning your anus into Better Homes and Gardens."

Warden opened his eyes, his pupils shifted involuntarily into hearts and his mouth went wibbly. "Ohhh my god, the way you're writhing around in my ass...Holy shit I don't think I've ever felt anything so amazing? Oh fuck..."

Stingray made a small sound in the back of his throat, barely audible, but both parties shot him a withering look. "Uh, do you mind? We're trying to have a moment here," said the Warden, voice sharp and indignant. 

"Brother, would you see that there are no further interruptions?" 

The other twin, who Stingray had somehow managed to forget about in the midst of things, teleported next to Stingray's head, blocking his view of the Warden. He looked down with a blank expression. 

"Hmm. I certainly have a lot of freedom here." He idly rapped his knuckles on the plate of Stingray's chastity belt before gliding his fingers up and down his thighs. Stingray whimpered and the twin took his hand away, grimacing slightly. "But I suppose I am to keep you quiet, and there is an obvious course of action to take." He phased his clothing off and straddled Stingray's face in one quick motion, facing his feet. His genitals weren't quite awake yet. "Lick," he said, low and commanding. 

Stingray eagerly obeyed, bringing his own lengthy tongue up against the twin's flat crotch and massaging it until the mass of tentacles began to slither its way out. The droplets of slime that hit his tongue were bitter and left a slight aftertaste of menthol, but before he had time to properly savor the flavor the large tentacle began sliding further into his mouth. He couldn't see much save a few wriggling tendrils which were dangerously close to dripping slime into his eyes, so he closed them and took a deep breath in.

The twin sitting on his face shifted and shimmied, biting back a trill as Stingray's teeth dragged across his genitals."Bite down hard three times in quick succession if you need to stop," he said, before thrusting his tentacle down, down into Stingray's throat. 

Stingray fought not to gag against the intrusion, especially when it tickled the back of his throat. He kept his breaths slow and steady through his nostrils even as tears pricked the corners of his eyes. He felt the twin move his hips above his face, grounded himself in the sensation of gloves pressed firmly into his chest for balance, and waggled his tongue around the massive tentacle stuffing his mouth. It slid in and out of his throat, oozing slime that caused him to occasionally cough and jab his fangs into the tendril.

Much to his surprise the twin seemed to only be further stirred by the sharp drag of his teeth, pressing his thighs tight into the sides of his face and emitting a low vibration. It was hard to hear much, hard to focus on anything other than his breathing and the slime dripping on his face and the smell of sweat and his throat stuffed full but he strained to listen to his boyfriend gasping and whining. The twin fucking his throat spoke. 

"It looks as though the Warden is about to come."

Much more muffled was his brother, replying "Yes. Come to his senses. Stingray is old news."

Stingray relished the gasp the twin let out as he scraped his teeth against the tentacle in a slow, deliberate motion, coinciding beautifully with a high and breathy moan that could only be the Warden coming. With some effort he managed to wrap the length of his tongue around the tendril, stretch his jaw a little more and swallow a few more inches down into his throat. The hands on his chest pressed down harder as he stroked his tongue up and down the length of the tentacle.

"Ha-ah! Ha ha. Stingray is trying to compensate."

"How amusing. Warden, would you like Stingray to see how it is done?" 

Stingray couldn't hear the Warden say anything, but the tentacle slid partway out of his throat and he opened his eyes. The twin had lifted one leg up and out in a partial side split, allowing Stingray to look at his boyfriend. Warden's chest was covered in a slick splatter of glittery rainbow cum, his limbs were noodly and his jaw was slack, a thin line of drool leaking from the corner of his mouth. The twin was still buried inside him, moving his hips in slow, measured thrusts. He smirked at Stingray before grasping at the Warden's cock and doing something with his tentacle that caused the Warden to yelp and erupt with another spurt of cum.

The twin kneeling over Stingray's face put his leg back down and thrust back into his throat. He strained to listen to the sounds of his boyfriend being fucked,  a symphony of breathless moans and cries that was beginning to twine with a bizarre and ethereal flute-like noise that was presumably the twins beginning to succumb to their arousal. Invigorated, Stingray flexed his throat and slid his teeth and tongue along the tendril with thorough intention.

It took a considerable amount of effort to focus as the twin's other tentacles began to lash and drip and drag across his face, but he kept his breath steady and his movements focused. Soon enough he heard the twin speak, voice shaky and broken up with gasps. 

"Warden, your pet is doing quite well. We may consider rewarding him if this behavior persists."

The Warden warbled an equally shaky "Is that so? Oooh....ooh God, yes, just like that...Stingray, if he doesn't come before I do then you're gonna...you're gonna have to eat every drop of cum out of my butthole!"

Stingray gulped reflexively, resulting in a shudder from the twin above him. Warden sounded incredibly close to coming already, so he did everything in his power to bring the twin over the edge, all tongue and fang and swallow and desperation.

It wasn't quite enough. Even with the twin chirping and shivering and lashing in his throat, he could hear the Warden gasp out in overstimulated orgasm once again, followed by a cacophonous beeping from the twin fucking him. 

The twin above him echoed the beep, and the tentacle abruptly slid out of his throat and splattered come over his face, onto his eyelids and in his mouth and nostrils and all the way down his chest. Stingray kept his eyes clenched shut, gasping for air and trying to cope with the indignity of drool and cum leaking down his chin. The tendrils gave one more stinging slap to his cheek before he felt them slide back up, leaving a disrespectful slime trail all the way up his face. He opened his eyes.

The twin teleported off of him and next to his brother. Both of them were gasping for air but the cruel smirks remained plastered across their faces. The Warden was a mess of his own cum and sweat and drool, and Stingray noted that his thighs were completely covered in clear, turquoise-tinted slime. 

The Warden inhaled deeply before speaking, voice breathless and uneven. "Oops! You lost the challenge! Say boys, if he can get me to come one more time by eating my butt, how about you give us that key?'

The twins nodded in unison. "That is fair."

"You heard them, Stingray." The Warden carefully sat up and crawled towards Stingray on wobbly legs, tummy slightly distended. Stingray stared wide-eyed at him, desperate with adoration and arousal, and as soon the Warden sat on his face he immediately went to work. There was come smeared all up the insides of his thighs, and Stingray made quick work of it. The Warden shifted as Stingray gently sucked the slime off his scrotum. By the time Stingray had cleaned his perineum and touched the tip of his thin tongue to his hole the Warden was panting. 

The inside of the Warden's ass was absolutely wrecked with alien dickslime. Just slipping his tongue inside resulted in a small stream dribbling down into his mouth. He slowly circled his tongue around, working more and more of the cum out. He savored the complex flavor, cool and bitter and crisp against the taste of hot flesh and sweat and the unique sweet essence of the Warden. His tongue was not nearly as long as the twins' horrifying crotchtentacles, but flexible enough that soon the Warden was quaking and gasping above him.

"Good boy, good boy, good pet...God, yes..." He craned his body forward, clinging to Stingray's head spine. His inner muscles squeezed at Stingray's tongue and helped get the last drops of cum into his desperate mouth. He cried out, and a drip of his own glistening Technicolor cum trickled down his dick and onto Stingray's nose. 

Warden pulled himself off of Stingray's face and collapsed next to him, trying to compose himself enough to speak, but the twins were already ahead of him. One of them stuck his tongue out and split it into a pair of sharp and nasty mandibles. The key dropped from his frightening mouthparts into his hand, and he offered it up to the Warden. "Shall you do the honors?"

"With pleasure." The Warden straightened up and untied Stingray's ankles. Stingray quivered with anticipation, breath shallow as the Warden unlocked his belt and gently shimmied it off. His cock was desperately hard and front hole wetter than he thought possible. 

"Wowee," said the Warden. "Looks like we did a number on him! What do you say, guys? Should we break the streak and let him come?"

Stingray tried desperately hard not to beg, grinding his teeth and breathing rapidly. The twins looked at each other with what felt like hours of consideration before saying. "Why not?" "It could be amusing."

"Alrighty!" said the Warden, untying Stingray's wrists. "Get to it, pal!"

Stingray immediately sat up and spread his legs wide. "Thank you, Warden sir" he said as he brought his hand down to his dick and stroked it cautiously between his forefinger and his thumb. He was boiling with arousal, so desperately turned on that just that light touch was painful and at terrible risk of causing him to come immediately. He glanced up to see the twins and the Warden all staring at him. The twins were snickering quietly at his predicament while the Warden just seemed curious as to what he would do next.

Thinking tactically he inserted the tip of one finger into his front hole and moved it carefully, finding a rhythm that was satisfying but not too overwhelming. He brought his other hand to his cock and stroked it very loosely between two knuckles. Everything was so hard and slippery and searing hot, and a high whine escaped his throat as he began to let himself finally sink into the sensation. Six months of chastity had taken their toll, and he knew the Warden would try to push a little longer next time, so he did his best to stay completely cognizant of the sensation even though he could hear the twins commenting wryly on the faces he made, feel the burning gaze of the Warden locked onto him.

He slid a little more of his finger inside, stroked himself faster, whimpered words of grattitude "Thank you Warden, thank you for being so charitable as to let me come, thank you so much..."

And all too soon his orgasm rolled through him, bright pulses of pure pleasure that forced him to keen desperately, hips bucking and hands shaking as he tried to memorize the feeling. The twins clapped and Warden whistled and his chest swelled with a sensation he couldn't quite name.

As soon as the final aftershock passed that feeling suddenly burst and sank, leaving a heavy emptiness in its stead. He felt cold, and small, and he was covered in smears of come and drool, and in that moment he wanted to sob. His lip wobbled and the Warden immediately snapped to attention.

"Whoa-ho, OK...sub drop. It's alright, Stingray, I'm here. Do you want the twins to be here too?"

Stingray nodded pitifully and held his arms out. "Can I....can someone please give me a hug?"

The twins teleported to his sides, phasing all the smears and stains away from his body, and crushed him up in a deliciously tight and warm embrace, and the Warden covered his front, arms draped over his shoulders as he peppered little kisses on Stingray's face. The tears that had been threatening the corners of Stingray's eyes finally streamed out as he took deep shuddering gulps of air. 

"Shooosh....it's ok, it's ok Stingray. We're all here. You did such a good job." The Warden kept kissing and soothing him until his breaths steadied. "Alright, I'm going to get up so I can get you something to drink. I'm not leaving the room, OK?"

Stingray nodded. The Warden stood up and opened a panel along the far wall where he kept cool drinks and sugary snacks. Stingray nuzzled harder into the twins' grasp and they stroked his face and shoulders. 

"Pressure stimulation?" "Touch starvation?" they asked, and Stingray nodded. "I'm sorry, I know it's silly, just....don't let go." 

The Warden came over with a bottle of aloe juice to soothe his fucked out throat and a little plate of ginger cookies. "Do you want something to drink? A snack?"

Stingray graciously accepted the juice and a few cookies. His tummy was still filled with cum and the heat of the twins' bodies was beginning to make him feel sleepy. He drifted for a long moment before he suddenly snapped his eyes open. He wriggled out of the twins' grasp and they teleported to the other end of the room, now fully dressed. 

"Is something the matter?" "Overstimulated?" they queried.

"He's fine," said the Warden. "He just needs some to process the scene. Do you want to stay here or go back to the cell, Stingray?"

"I'm quite alright," Stingray huffed. "I just need a nap here while you clean my belt and then I have a little game night to attend to. Sound good, Warden?"

The Warden rolled his eyes at Stingray's commanding tone, but glanced at the twins. "Thanks, guys. Next time?"

"See you soon, Warden." "We will be keeping an eye on you, Stingray." They teleported off without much fanfare, and the Warden tucked Stingray into the big bed. 

"I love you, Stingray. You know that, right?" He caressed his boyfriend's golden cheek as he spoke. 

"Pfft, of course. If you didn't love me, you wouldn't indulge me so." Stingray responded. "Now let me sleep."

And so he passed out in blessed silence, sweet relief and the loving warm sting of humiliation. Jean and Paul were going to be so jealous. 


End file.
